#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/45/7204597.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204597
loop_
_publ_author_name
'Baskar Raj, S.'
'Sethuraman, V.'
'Francis, S.'
'Hemamalini, M.'
'Muthiah, P. Thomas'
'Bocelli, G.'
'Cantoni, A.'
'Rychlewska, U.'
'Warzajtis, B.'
_publ_section_title
;
 Supramolecular organisation via hydrogen bonding in trimethoprim
 sulfonate salts
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              70
_journal_paper_doi               10.1039/b300126a
_journal_volume                  5
_journal_year                    2003
_chemical_formula_moiety         'C14H19N4O3,C7H5O6S, 2H2O'
_chemical_formula_sum            'C21 H28 N4 O11 S'
_chemical_formula_weight         544.53
_chemical_name_common
;
2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidinium 3-
carboxy-4-hydroxybenzene sulfonate dihydrate
;
_chemical_name_systematic
;
2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidinium 
3-carboxy-4-hydroxybenzene
sulfonate dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.442(2)
_cell_length_b                   18.769(3)
_cell_length_c                   12.783(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      2.0
_cell_volume                     2504.4(10)
_computing_cell_refinement       'MolEN (Fair, 1990)'
_computing_data_collection       'MolEN (Fair, 1990)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'PLATON (Spek, 1997)'
_computing_publication_material  'PLATON (Spek, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type  'Bruker AXS smart with CCD'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1402
_diffrn_reflns_av_sigmaI/netI    0.2647
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21406
_diffrn_reflns_theta_full        28.43
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'plate like'
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.793
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5595
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.796
_refine_ls_R_factor_all          0.2598
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0106P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                1718
_reflns_number_total             5595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b300126a.txt
_cod_data_source_block           compound_4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2504.4(8)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7204597
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O -0.0958(3) 0.19659(15) 0.3823(2) 0.0662(10) Uani 1 1 d . . .
O8 O -0.0679(3) 0.20271(17) 0.0274(2) 0.0575(9) Uani 1 1 d . . .
S S -0.05961(12) 0.12314(7) 0.41811(9) 0.0487(3) Uani 1 1 d . . .
O5 O 0.0462(3) 0.11843(14) 0.53221(19) 0.0605(8) Uani 1 1 d . . .
C23 C 0.0026(4) 0.1467(2) 0.0376(3) 0.0442(11) Uani 1 1 d . . .
C22 C -0.0224(4) 0.1275(2) 0.2208(3) 0.0412(11) Uani 1 1 d . . .
O9 O 0.0492(3) 0.13036(14) -0.0299(2) 0.0591(9) Uani 1 1 d . . .
O1W O 0.3811(4) 0.5444(2) 0.0234(3) 0.1187(14) Uani 1 1 d D . .
O4 O -0.1660(3) 0.07848(16) 0.4105(2) 0.0665(9) Uani 1 1 d . . .
C17 C 0.0247(4) 0.1035(2) 0.1417(3) 0.0378(11) Uani 1 1 d . . .
C21 C 0.0009(4) 0.0898(2) 0.3192(3) 0.0368(10) Uani 1 1 d . . .
C18 C 0.0950(4) 0.0411(2) 0.1640(3) 0.0468(11) Uani 1 1 d . . .
C20 C 0.0685(4) 0.0271(2) 0.3414(3) 0.0470(12) Uani 1 1 d . . .
C16 C 0.2820(6) 0.4967(3) 0.3534(5) 0.0680(17) Uani 1 1 d . . .
O7 O 0.1477(3) 0.01546(16) 0.0931(3) 0.0652(10) Uani 1 1 d D . .
C19 C 0.1164(5) 0.0029(2) 0.2640(4) 0.0532(14) Uani 1 1 d . . .
O1 O 0.3651(3) 0.44365(16) 0.3426(2) 0.0592(9) Uani 1 1 d . . .
O2W O 0.3237(4) 0.4165(2) 0.1051(3) 0.0739(10) Uani 1 1 d D . .
C15 C 0.6296(4) 0.3829(3) 0.3173(3) 0.0871(17) Uani 1 1 d . . .
H15A H 0.6394 0.4279 0.3558 0.131 Uiso 1 1 calc R . .
H15B H 0.6196 0.3908 0.2399 0.131 Uiso 1 1 calc R . .
H15C H 0.7042 0.3542 0.3568 0.131 Uiso 1 1 calc R . .
C12 C 0.4270(4) 0.4000(2) 0.4352(3) 0.0420(11) Uani 1 1 d . . .
C13 C 0.4132(4) 0.4046(2) 0.5378(3) 0.0452(12) Uani 1 1 d . . .
O2 O 0.5199(3) 0.34743(14) 0.3166(2) 0.0548(8) Uani 1 1 d . . .
C11 C 0.5098(4) 0.3512(2) 0.4219(3) 0.0432(11) Uani 1 1 d . . .
C7 C 0.4680(5) 0.3621(3) 0.7386(4) 0.0502(14) Uani 1 1 d . . .
C8 C 0.4816(4) 0.3582(2) 0.6263(3) 0.0436(11) Uani 1 1 d . . .
N4 N 0.3919(4) 0.3584(2) 0.9266(3) 0.0555(12) Uani 1 1 d . . .
C10 C 0.5772(4) 0.3041(2) 0.5092(4) 0.0451(11) Uani 1 1 d . . .
C9 C 0.5649(4) 0.3081(2) 0.6131(3) 0.0459(12) Uani 1 1 d . . .
C5 C 0.3650(4) 0.3138(2) 0.7441(3) 0.0394(11) Uani 1 1 d . . .
C4 C 0.3324(4) 0.3134(2) 0.8416(3) 0.0418(11) Uani 1 1 d . . .
O3 O 0.6530(3) 0.25642(16) 0.4860(2) 0.0602(8) Uani 1 1 d . . .
C14 C 0.7243(7) 0.2066(3) 0.5738(7) 0.0694(18) Uani 1 1 d . . .
N3 N 0.2468(3) 0.26951(19) 0.8536(3) 0.0461(10) Uani 1 1 d . . .
C6 C 0.2974(4) 0.2685(2) 0.6606(4) 0.0458(12) Uani 1 1 d . . .
N1 N 0.2069(4) 0.2256(2) 0.6702(3) 0.0476(11) Uani 1 1 d . . .
C2 C 0.1856(4) 0.2257(2) 0.7681(4) 0.0460(12) Uani 1 1 d . . .
N2 N 0.0979(4) 0.1808(3) 0.7723(4) 0.0643(14) Uani 1 1 d . . .
H1 H 0.670(4) 0.176(2) 0.593(3) 0.081(17) Uiso 1 1 d . . .
H2 H 0.358(3) 0.4368(14) 0.549(2) 0.014(9) Uiso 1 1 d . . .
H3 H 0.252(4) 0.5193(19) 0.287(3) 0.054(14) Uiso 1 1 d . . .
H4 H 0.442(3) 0.4066(16) 0.748(2) 0.021(10) Uiso 1 1 d . . .
H5 H -0.070(3) 0.1679(14) 0.206(2) 0.012(9) Uiso 1 1 d . . .
H6 H 0.308(3) 0.2651(17) 0.596(3) 0.045(12) Uiso 1 1 d . . .
H7 H 0.203(4) 0.4739(19) 0.358(3) 0.071(16) Uiso 1 1 d . . .
H2W1 H 0.480(3) 0.519(2) 0.050(3) 0.095(18) Uiso 1 1 d D . .
H8 H 0.163(3) -0.0390(17) 0.279(3) 0.049(13) Uiso 1 1 d . . .
H9 H 0.083(3) -0.0035(16) 0.407(3) 0.042(11) Uiso 1 1 d . . .
H10 H 0.541(3) 0.3449(18) 0.798(3) 0.053(14) Uiso 1 1 d . . .
H12 H 0.361(4) 0.362(2) 0.981(3) 0.085(17) Uiso 1 1 d . . .
H13 H 0.609(3) 0.2711(18) 0.674(3) 0.063(13) Uiso 1 1 d . . .
H15 H 0.336(4) 0.528(2) 0.423(3) 0.11(2) Uiso 1 1 d . . .
H1W2 H 0.356(4) 0.398(2) 0.177(2) 0.12(2) Uiso 1 1 d D . .
H16 H 0.057(3) 0.1501(18) 0.714(3) 0.051(14) Uiso 1 1 d . . .
H17 H 0.163(4) 0.1914(18) 0.622(3) 0.046(13) Uiso 1 1 d . . .
H18 H 0.769(5) 0.178(2) 0.535(4) 0.14(2) Uiso 1 1 d . . .
H2W2 H 0.240(3) 0.430(3) 0.093(4) 0.19(3) Uiso 1 1 d D . .
H20 H 0.462(3) 0.3838(19) 0.935(3) 0.044(14) Uiso 1 1 d . . .
H21 H -0.069(4) 0.240(2) -0.033(4) 0.13(2) Uiso 1 1 d . . .
H22 H 0.077(4) 0.181(3) 0.821(3) 0.09(2) Uiso 1 1 d . . .
H23 H 0.114(4) 0.0481(17) 0.031(2) 0.069(15) Uiso 1 1 d D . .
H24 H 0.775(5) 0.229(3) 0.634(4) 0.10(3) Uiso 1 1 d . . .
H1W1 H 0.368(5) 0.503(3) 0.073(6) 0.34(6) Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S O6 113.80(19) . . ?
O4 S O5 111.13(16) . . ?
O6 S O5 112.43(17) . . ?
O4 S C21 107.96(16) . . ?
O6 S C21 104.60(17) . . ?
O5 S C21 106.32(18) . . ?
O9 C23 O8 124.3(4) . . ?
O9 C23 C17 122.0(4) . . ?
O8 C23 C17 113.7(4) . . ?
C21 C22 C17 120.5(4) . . ?
C18 C17 C22 119.2(4) . . ?
C18 C17 C23 121.1(4) . . ?
C22 C17 C23 119.7(4) . . ?
C22 C21 C20 120.9(4) . . ?
C22 C21 S 118.8(3) . . ?
C20 C21 S 120.3(3) . . ?
O7 C18 C17 122.7(4) . . ?
O7 C18 C19 117.8(4) . . ?
C17 C18 C19 119.5(4) . . ?
C21 C20 C19 119.1(4) . . ?
C20 C19 C18 120.8(4) . . ?
C12 O1 C16 117.6(4) . . ?
O1 C12 C11 115.3(4) . . ?
O1 C12 C13 124.1(4) . . ?
C11 C12 C13 120.6(4) . . ?
C12 C13 C8 119.2(4) . . ?
C11 O2 C15 113.0(3) . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 O2 119.0(4) . . ?
C10 C11 O2 120.3(4) . . ?
C8 C7 C5 113.7(4) . . ?
C13 C8 C9 120.6(4) . . ?
C13 C8 C7 120.1(4) . . ?
C9 C8 C7 119.3(4) . . ?
O3 C10 C11 116.0(4) . . ?
O3 C10 C9 124.4(4) . . ?
C11 C10 C9 119.5(4) . . ?
C10 C9 C8 119.5(4) . . ?
C6 C5 C4 114.7(4) . . ?
C6 C5 C7 123.5(4) . . ?
C4 C5 C7 121.8(4) . . ?
N4 C4 N3 117.0(4) . . ?
N4 C4 C5 118.7(4) . . ?
N3 C4 C5 124.3(4) . . ?
C10 O3 C14 117.9(4) . . ?
C2 N3 C4 117.1(4) . . ?
C5 C6 N1 121.3(4) . . ?
C6 N1 C2 120.6(4) . . ?
N3 C2 N2 121.1(4) . . ?
N3 C2 N1 121.8(4) . . ?
N2 C2 N1 117.1(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 S 1.458(3) . ?
O8 C23 1.299(4) . ?
S O4 1.448(3) . ?
S O5 1.468(3) . ?
S C21 1.785(3) . ?
C23 O9 1.224(4) . ?
C23 C17 1.490(5) . ?
C22 C21 1.371(4) . ?
C22 C17 1.401(5) . ?
C17 C18 1.382(5) . ?
C21 C20 1.372(5) . ?
C18 O7 1.365(4) . ?
C18 C19 1.398(5) . ?
C20 C19 1.389(5) . ?
C16 O1 1.421(6) . ?
O1 C12 1.374(4) . ?
C15 O2 1.418(4) . ?
C12 C11 1.377(5) . ?
C12 C13 1.386(4) . ?
C13 C8 1.388(5) . ?
O2 C11 1.399(4) . ?
C11 C10 1.385(5) . ?
C7 C8 1.507(5) . ?
C7 C5 1.511(6) . ?
C8 C9 1.396(5) . ?
N4 C4 1.323(5) . ?
C10 O3 1.360(4) . ?
C10 C9 1.394(5) . ?
C5 C6 1.336(5) . ?
C5 C4 1.440(5) . ?
C4 N3 1.337(5) . ?
O3 C14 1.431(6) . ?
N3 C2 1.316(5) . ?
C6 N1 1.357(5) . ?
N1 C2 1.370(4) . ?
C2 N2 1.328(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149572
